$145+ Cheap flights from O'Hare Intl (ORD) to Portland, ME (PWM)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/9. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — PWM
Dec 4 — Dec 111
Round-trip
1 adult, Economy
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Find cheap flights from O'Hare Intl to Portland with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Chicago O'Hare Intl to Portland are usually found in May or April, booked 47 days in advance, depart on a Wednesday or Saturday and return on a Wednesday
Cheap flight deals from O'Hare Intl to Portland
Cheapest
Best
Last-minute
One-way
Cheapest flights from O'Hare Intl to PortlandExplore the most affordable flight options available from O'Hare Intl to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 4, 2026.
Explore the most affordable flight options available from O'Hare Intl to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 4, 2026.
This Delta deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/253:59 pm -
1 stop6h 32m
Fri 12/44:00 pm -
1 stop6h 36m
Deal found 11/2![Delta logo]()
$334
This Delta deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/46:03 pm -
1 stop5h 18m
Sun 12/66:00 am -
2 stops11h 43m
Deal found 11/4![Delta logo]()
$344
This American Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/252:52 pm -
1 stop6h 47m
Fri 12/412:44 pm -
Nonstop3h 16m
Deal found 11/2![American Airlines logo]()
$349
This United Airlines deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/206:18 pm -
Nonstop2h 34m
Fri 11/275:30 am -
1 stop5h 15m
Deal found 10/30![United Airlines logo]()
$353
This United Airlines deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/45:50 pm -
Nonstop2h 39m
Sun 12/66:00 am -
1 stop5h 46m
Deal found 11/4![United Airlines logo]()
$355
This Delta deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/188:39 am -
1 stop6h 32m
Thu 12/312:09 pm -
1 stop8h 06m
Deal found 11/1![Delta logo]()
$359
This United Airlines deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/246:10 pm -
1 stop4h 49m
Fri 1/19:48 am -
1 stop5h 41m
Deal found 11/4![United Airlines logo]()
$362
This United Airlines deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/234:40 pm -
1 stop5h 41m
Fri 11/275:30 am -
1 stop5h 15m
Deal found 10/30![United Airlines logo]()
$363
This Delta deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/237:05 am -
1 stop3h 53m
Sat 12/56:12 am -
2 stops8h 44m
Deal found 11/4![Delta logo]()
$364
This American Airlines deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/188:30 am -
Nonstop2h 28m
Fri 11/278:00 am -
1 stop7h 25m
Deal found 11/1![American Airlines logo]()
$369
This United Airlines deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1811:59 am -
Nonstop2h 32m
Fri 1/18:00 am -
Nonstop3h 15m
Deal found 10/31![United Airlines logo]()
$375
Best flights from O'Hare Intl to PortlandDiscover carefully curated flight deals from O'Hare Intl to Portland that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 4, 2026.
Discover carefully curated flight deals from O'Hare Intl to Portland that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 4, 2026.
This Delta deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/253:59 pm -
1 stop6h 32m
Fri 12/412:49 pm -
2 stops7h 56m
Deal found 11/2![Delta logo]()
$339
This United Airlines deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/246:10 pm -
1 stop4h 49m
Thu 12/314:28 pm -
Nonstop3h 12m
Deal found 11/3![United Airlines logo]()
$349
This Delta deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/195:30 am -
1 stop6h 31m
Sun 11/226:00 am -
1 stop7h 46m
Deal found 11/1![Delta logo]()
$379
This United Airlines deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1310:50 am -
Nonstop2h 26m
Mon 11/165:08 pm -
Nonstop2h 57m
Deal found 10/30![United Airlines logo]()
$379
This Delta deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/1611:35 am -
2 stops10h 46m
Wed 11/1812:45 pm -
1 stop4h 33m
Deal found 11/1![Delta logo]()
$404
This United Airlines deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/211:55 am -
1 stop6h 30m
Sat 12/54:47 pm -
Nonstop3h 13m
Deal found 11/3![United Airlines logo]()
$424
This Delta deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/127:05 am -
1 stop3h 53m
Sun 11/156:00 am -
1 stop7h 20m
Deal found 11/1![Delta logo]()
$419
This United Airlines deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/1211:59 am -
Nonstop2h 39m
Sat 1/27:44 pm -
1 stop5h 17m
Deal found 11/3![United Airlines logo]()
$424
This Delta deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/76:00 pm -
1 stop5h 10m
Tue 11/102:05 pm -
1 stop7h 44m
Deal found 10/31![Delta logo]()
$439
This Delta deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/710:05 am -
1 stop4h 50m
Wed 11/114:03 pm -
2 stops8h 51m
Deal found 11/2![Delta logo]()
$444
Last-minute flights from O'Hare Intl to PortlandDiscover last-minute flight deals from O'Hare Intl to Portland. Data last updated November 4, 2026 and is based on user searches.
Discover last-minute flight deals from O'Hare Intl to Portland. Data last updated November 4, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/188:30 am -
Nonstop2h 28m
Fri 11/278:00 am -
1 stop7h 25m
Deal found 11/1![American Airlines logo]()
$369
This United Airlines deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/206:18 pm -
Nonstop2h 34m
Fri 11/275:30 am -
1 stop5h 15m
Deal found 10/30![United Airlines logo]()
$353
This United Airlines deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/234:40 pm -
1 stop5h 41m
Fri 11/275:30 am -
1 stop5h 15m
Deal found 10/30![United Airlines logo]()
$363
This Delta deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/237:05 am -
1 stop3h 53m
Sat 12/56:12 am -
2 stops8h 44m
Deal found 11/4![Delta logo]()
$364
This Delta deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/253:59 pm -
1 stop6h 32m
Fri 12/44:00 pm -
1 stop6h 36m
Deal found 11/2![Delta logo]()
$334
This American Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/252:52 pm -
1 stop6h 47m
Fri 12/412:44 pm -
Nonstop3h 16m
Deal found 11/2![American Airlines logo]()
$349
This Delta deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/46:03 pm -
1 stop5h 18m
Sun 12/66:00 am -
2 stops11h 43m
Deal found 11/4![Delta logo]()
$344
This United Airlines deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/45:50 pm -
Nonstop2h 39m
Sun 12/66:00 am -
1 stop5h 46m
Deal found 11/4![United Airlines logo]()
$355
This Delta deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/188:39 am -
1 stop6h 32m
Tue 12/295:35 am -
1 stop6h 44m
Deal found 11/1![Delta logo]()
$359
This United Airlines deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1811:59 am -
Nonstop2h 32m
Fri 1/18:00 am -
Nonstop3h 15m
Deal found 10/31![United Airlines logo]()
$375
This United Airlines deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/246:10 pm -
1 stop4h 49m
Fri 1/19:48 am -
1 stop5h 41m
Deal found 11/4![United Airlines logo]()
$362
One-way flights from O'Hare Intl to PortlandSearch for one-way flight options from O'Hare Intl to Portland. Find affordable one-way fares based on user searches. Data last updated November 4, 2026.
Search for one-way flight options from O'Hare Intl to Portland. Find affordable one-way fares based on user searches. Data last updated November 4, 2026.
This American Airlines deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/98:26 am -
Nonstop2h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![American Airlines logo]()
$145
This Delta deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/98:50 am -
1 stop6h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Delta logo]()
$155
This Kiwi.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/94:00 pm -
2 stops40h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Multiple Airlines logo]()
$159
This Delta deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/1311:20 am -
2 stops10h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Delta logo]()
$160
This American Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/268:30 am -
Nonstop2h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![American Airlines logo]()
$170
This Kiwi.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/13:55 pm -
2 stops18h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Multiple Airlines logo]()
$176
This United Airlines deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/256:18 pm -
Nonstop2h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![United Airlines logo]()
$177
This Delta deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/266:00 am -
2 stops8h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![Delta logo]()
$185
Find flight deals from O'Hare Intl to Portland
Discover tips and strategies to find the most affordable flight options for your journey from O'Hare Intl (ORD) to Portland (PWM). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated November 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $289 (United Airlines) |
One-way from | $145 (American Airlines) |
Popular in | November |
Cheapest in | May |
Average price | $480 |
Good round-trip deal | $444 or less |
Good one-way deal | $258 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from O'Hare Intl to Portland that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated November 4, 2026.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Portland that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoPortland
ORD Chicago O'Hare Intl - PWM Portland
ORDPWM
Chicago O'Hare Intl
Wed 12/9
8:50 am-4:39 pm
1 stop6h 49m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$155
ChicagoPortland
ORD Chicago O'Hare Intl - PWM Portland
ORDPWM
Chicago O'Hare Intl
Wed 11/25
6:18 pm-9:51 pm
Nonstop2h 33m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$177
ChicagoPortland
ORD Chicago O'Hare Intl - PWM Portland
ORDPWM
Chicago O'Hare Intl
Thu 11/26
7:00 am-3:38 pm
1 stop7h 38m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$180
ChicagoPortland
ORD Chicago O'Hare Intl - PWM Portland
ORDPWM
Chicago O'Hare Intl
Sun 11/22
5:30 am-1:01 pm
1 stop6h 31m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$180
ChicagoPortland
ORD Chicago O'Hare Intl - PWM Portland
ORDPWM
Chicago O'Hare Intl
Mon 11/23
5:29 pm-10:56 pm
1 stop4h 27m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$205
ChicagoPortland
ORD Chicago O'Hare Intl - PWM Portland
ORDPWM
Chicago O'Hare Intl
Sat 11/21
12:38 pm-11:31 pm
2 stops9h 53m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$205
ChicagoPortland
ORD Chicago O'Hare Intl - PWM Portland
ORDPWM
Chicago O'Hare Intl
Mon 11/16
11:35 am-11:21 pm
2 stops10h 46m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$205
ChicagoPortland
ORD Chicago O'Hare Intl - PWM Portland
ORDPWM
Chicago O'Hare Intl
Tue 11/24
6:18 pm-9:51 pm
Nonstop2h 33m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$209
ChicagoPortland
ORD Chicago O'Hare Intl - PWM Portland
ORDPWM
Chicago O'Hare Intl
Tue 11/10
6:18 pm-9:51 pm
Nonstop2h 33m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$210
Quickest round-trip
ChicagoPortland
ORD Chicago O'Hare Intl - PWM Portland
ORDPWM
Chicago O'Hare Intl
Fri 12/18
11:59 am-3:31 pm
Nonstop2h 32m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$210
Showing 1-10 of 21 resultsSorted by cheapest first
Compare providers for flights from O'Hare Intl to Portland
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from O'Hare Intl to Portland in November.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago O'Hare Intl Airport-Portland, Maine flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago O'Hare Intl Airport-Portland, Maine flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago O'Hare Intl Airport-Portland, Maine flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago O'Hare Intl Airport-Portland, Maine flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago O'Hare Intl Airport-Portland, Maine flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from O'Hare Intl to Portland
Have a flexible travel schedule? Discover the best time to fly to Portland from O'Hare Intl with our price prediction graph.
ORD-PWM
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago O'Hare Intl Airport to Portland
Prices
Airlines
Delays
How far ahead should I book a flight from Chicago O'Hare Intl Airport to Portland, Maine?
To ensure you get the cheapest price possible for a flight from Chicago O'Hare Intl Airport to Portland, Maine, you should look to book at least 46 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Portland, Maine?
Currently, May is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Portland, Maine (average of $319). Flying from Chicago O'Hare Intl Airport to Portland, Maine in November is currently the most expensive (average of $480). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from ORD to PWM?
Find hourly flight availability from O'Hare Intl to Portland. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 4, 2026.
When flying from Chicago O'Hare Intl Airport to Portland, Maine, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 23% versus a flight in the afternoon.
What is the cheapest day to fly from Chicago O'Hare Intl Airport to Portland, Maine?
Use this chart to determine the cheapest time to fly round-trip from O'Hare Intl to Portland. Price data was last updated on October 31, 2026.
Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to Portland, Maine flight should consider departing on Saturday at noon when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
How often are flights from Chicago to Portland delayed?
About 18% of weekly flights between Chicago and Portland have experienced delays in the past year, with the average delay time being 139 minutes.
What is the most punctual flight time for Chicago to Portland flights?
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving at night tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Tuesday tends to have the lowest number of delays on this route, whereas Friday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Chicago to Portland flights?
Over the last year, American Airlines have had the lowest number of delays on this route, with just 17% of flights being delayed.
Reviews of airlines servicing Portland
Get insights into the airlines that provide service to Portland. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Portland. Reviews last updated November 4, 2026.
Read through reviews of airlines operating flights from Chicago O'Hare Intl Airport to Portland, such as United Airlines and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Comfort
7.3
Boarding
7.7
Food
6.7
Crew
8.1
Entertainment
7.1
Overall
7.3
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Comfort
7.3
Boarding
7.7
Food
6.7
Crew
8.1
Entertainment
7.1
Overall
7.3
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Comfort
7.3
Boarding
7.7
Food
6.7
Crew
8.1
Entertainment
7.1
Overall
7.3
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Related info for your journey
Find useful and relevant information for your journey from O'Hare Intl to Portland. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Portland?
Book flights to Portland if you plan to visit one of these locationsLewiston
North Conway
Brunswick
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Top 2 airlines flying from O'Hare Intl to Portland
Discover the top 2 airlines that operate flights from O'Hare Intl to Portland. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated November 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$229 | Average$371 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$234 | Average$391 | FlexibilityNo cancel fee | On-time69% |